Vacation Rentals & Villas in Windsor Hills Resort

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6,238 Houses

Wow Factor-Interior Designers Own 5 bed/5bath Home

Kissimmee house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

Price per night from

$224

Windsor Hills 5BR/ 5BA SF Pool Villa,3MI to disney

Kissimmee villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

Responds fast! avg. 3 hours 33 minutes

Price per night from

$247

MINUTES TO WALT DISNEY WORLD'S FRONT GATE

Kissimmee condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$160

Pooh's Palace in Windsor Hills

Kissimmee villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

Price per night from

$516

Renting condo,One mile to Disney's Animal Kingdom

Kissimmee condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$104

Windsor Hills Retreat Villa

Kissimmee villa

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 12

Price per night from

$458

Windsor Hills Disney Townhouse, Newly Redecorated

Kissimmee townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$160

Great rentals within 20 miles that match your search

Bonnet Creek Resort ツ 1BR SLEEPS 4 Wyndham Orlando Condo Rental!

Orlando condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$91

Orange Lake Resort Villa, 2br/2ba (Kissimmee)

Orlando villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$229

Cozy One Bedroom Villa in Gorgeous Resort & Spa

Kissimmee villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$180

Two-Bedroom Villa

Orlando villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$492

Responds fast! avg. 2 hours 44 minutes

Price per night from

$344

3 Bedrooms / 2 Bathrooms / Seven Dwarfs (10-105 LC)

Kissimmee house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

Responds fast! avg. 3 hours 26 minutes

Price per night from

$119

7 Bedrooms / 5 Bathrooms / Solterra (4103 OD)

Davenport house

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 22

Responds fast! avg. 3 hours 26 minutes

Price per night from

$214

Premium Kissimmee Timeshare rental

Kissimmee villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$328

Vacation Villages at Parkway

Kissimmee apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$115

Prestige 3: New Lux Home, South Fc Lake View, Pool

Kissimmee villa

  • 8 bedrooms
  • 6 bathrooms
  • sleeps 20

Price per night from

$688

3 bedroom Townhouse close to Disney

Kissimmee townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$339

Smoky Mountain 5 Star resort

Orlando condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$230

Orlando Florida - Westgate Lakes Resort!

Orlando condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$152

Four Bedroom home near Disney/Orlando

Kissimmee house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$121

8br/6ba pool villa from $260/nt ,Close to Disney

Kissimmee house

  • 8 bedrooms
  • 6 bathrooms
  • sleeps 18

“Mrs” Me and my family really enjoyed staying at the property rental it was ever thing we need in a vaction rental.

Responds fast! avg. 1 hour 19 minutes

Price per night from

$344

Seven Palms at Waterford Way

Kissimmee house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Decent” Nice for a gate away. The rugs in the bathrooms need to be washed and the b es were uncomfortable. Location was great near everything.

Responds fast! avg. 3 hours 32 minutes

Price per night from

$184

A week of dream in a resort

Orlando house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$200

1 Week Rental in Orlando, FL 2 Bdm Deluxe Villa Close to Theme Parks

Orlando villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$196

Beautiful 2 BR, 2BA Orlando Florida!

Kissimmee condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$492

Wyndham Bonnet Creek Florida at Disney

Buena Ventura Lakes condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 1 minutes

Price per night from

$101

Responds fast! avg. 30 minutes

Price per night from

$114

Responds fast! avg. 30 minutes

Price per night from

$160

1-bedroom / 1-bath Sleeps 4 in Orlando - 1 week

Williamsburg apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$99

Lovely villa on Emerald Island-4 miles from Disney

Kissimmee villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$173

Disney Area Villa in gated Aviana Resort

Orlando villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

“Mrs” This rental was clean and neat. It had great amenities and my kids love the pool and spa. The play room in the garage made it perfect for my kids when they ran out of energy from the pool. The staff was friendly and helpful. I would defiantly recommend this unit to anyone.

Responds fast! avg. 3 hours 28 minutes

Price per night from

$172

Marriott's Sabal Palms

Orlando condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$459

Windsor Palms 4/3 Pr. Pl., Hot Tub, Jacuzzi/Games

Kissimmee house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

“Amazing house!” We have amazing family time! This house is excellent with great location! We'll be back soon! I recommend

Price per night from

$177

Stunning Disney Vacation Rental Villa

Kissimmee house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$172

Bella Vida Resort 4 Bdrm Private Home

Kissimmee house

  • 6 bedrooms
  • 3 bathrooms
  • sleeps 10

Responds fast! avg. 2 hours 19 minutes

Price per night from

$190

$1250+fees sleep 6, available Dec 24-Dec 31, 2022 Resort Fantasy World II

Kissimmee villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$194

Spacious villa near Disney

Four Corners house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 11

Responds fast! avg. 29 minutes

Price per night from

$114

Viewing 38 of 6,238
rentals in Windsor Hills Resort

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Top Destination reviews

Windsor Hills 5BR/ 5BA SF Pool Villa,3MI to disney
we loved this house didn't want to leave

The house was fully stocked for a large family. Loved the location. Had plenty to do on site. House was clean. We felt safe being in a gated security resort. Loved the pool and hot tub after long days at the parks. Jennifer was very helpful and responsive to all my questions before we arrived to the property. Would not hesitate to rent again. Cons on property the strollers we were going to use were broken, maybe could use some new frying pans.Some of the screens on the screened in patio was missing and the patio door the track seemed bent it was hard to close.Just those few things that were minor did not really affect our stay too much.see more
Renting condo,One mile to Disney's Animal Kingdom
Christmas Vaca

The location waa excellent just a 5 minute drive from Disney the apartment was clean and nicely decorated.There was no soap or extra toiletries so bring your own..Booking was easy..The only problem was when we arrived I was emailed the gate code and door code which were both wrong luckily the emergency number was readily available..The next day the door code was changed to something else again but we were quickly texted back with a workable code..Other than that the Stay was great!see more

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